My outline for the project would be to blend the two Glee tracks and comedy track to create a 2-3 minute cheerful loop (with the comedy track acting as a sort of ironic play on what we are doing with the music), with bells, santa laughs, and other festive samples covering the transitions.
I would then create a dynamic push in to the more epic Christmas suite, and create a transition at the end that perfectly looped back in to the Glee/comedy track beginning, thus creating a continuous loop with no breaks in play. I could utilise a radio style countdown at the beginning or end to build a sense of expectancy also.
I have produced and remixed a number of bands so I would be able to complete this project effectively utilising Logic Pro X and my own sample libraries.
If you wish to discuss any ideas further I am eager to discuss.
All the best
Josh